Those who know little about Yiddish often associate it with humor. But most Yiddish literature isn’t particularly funny except in a horrible, un-American way: comically-told plots in which people suffer terribly or die horrible deaths. Even the relentlessly upbeat Sholem Aleichem, whose Tevye stories inspired the relentlessly upbeat Fiddler on the Roof, fits this pattern: In the original, Golde and Motl both drop dead and Shprintze drowns herself, none of which made it to Broadway. Call it anti-redemptive comedy, the inverse of the Western-Christian comic storyline where winsome protagonists find love and grace. Their Yiddish counterparts instead find doom and more doom.This depressing aspect of Yiddish literature has a profound source beyond Jewish historical realities: Jewish tradition is fundamentally skeptical of art, and consequently, Yiddish literature’s greatest humor is really humor about literature’s supposed redemptive powers. Consider one of modern Yiddish literature’s foundational novels, Mendele the Book Peddler’s Travels of Benjamin the Third—a parody of classic Hebrew travelogues describing Jewish merchants’ voyages around the medieval world. Or, as its Russian-translation title announces, The Jewish Don Quixote.Mendele the Book Peddler is the pseudonym—or more accurately the persona, since he often appears as a character—of S.Y. Abramovitsh (1836-1917), a man whose biography would be implausible as fiction. A child prodigy who could identify each word touched by a pin stuck through a volume of Talmud, Abramovitsh was orphaned in a Belarusian shtetl as a young teenager and set out for greener pastures in Ukraine. He was soon abducted by a criminal gang, whose leader passed him off as his genius son in order to con wealthy families into marrying their daughters to Abramovitsh; after collecting the dowry, the gang skipped town to repeat the trick.Once Abramovitsh escaped into actual marriage, he spent decades in poverty but eventually became a founder of both modern Yiddish and Hebrew literature. His early works satirized corrupt Jewish communities in the hope of reforming them; Abramovitsh initially believed that assimilation would eradicate anti-Semitism. The brutal 1871 pogrom in Odessa, a cosmopolitan city with a highly assimilated Jewish population, changed his mind. His later novels are deeply absurdist works that present European Jews as trapped in a cycle of naïveté and doom. Not coincidentally, they’re also hilarious.Travels of Benjamin the Third (1878; available in English in Tales of Mendele the Book Peddler, trans. Hillel Halkin, and quoted here) is about a pair of shtetl idiots who decide to journey to the Promised Land and end up walking around the block. Like Don Quixote, our leading idiot, Benjamin, is driven mad by books—in his case, medieval travelogues of the Land of Israel. His Sancho Panza is Sendrel, a loser whose wife routinely beats him. Sendrel wants to escape violence, while Benjamin is inspired by proto-Zionist delusion; both motivations, which are the twin engines of modern Jewish history, are played for laughs. When they embark on their “expedition”—which begins at the town windmill, naturally—only Sendrel thinks to pack food. Benjamin brings The Praises of Jerusalem to use as a map. As he tells Sendrel, “You’ll be in charge of the physical half of our expedition, eating and drinking and all that, and I’ll be in charge of the mental half.” Sendrel, the chump, is delighted, and the two set off.Half the book’s humor comes from Abramovitsh’s sendup of the shtetl’s extreme poverty and its debased inhabitants, which he paints as though describing Oriental wonders. Of one dilapidated town, Benjamin announces: “Architecturally, there is plentiful evidence of antiquity.” An entire chapter delineates the various types of garbage flowing into a local bog. People are likewise anthropologically described: “Teterevke, Benjamin relates, is inhabited by a large number of Jews … traceable to diverse uprooted tribes that chanced to settle in one place, as is evidenced by the fact that they have to this day so little to do with each other that, if one of them falls in the street, the others, strange to say, will refuse to help him up even should his life depend on it.”Abramovitsh occasionally descends into the slapstick or burlesque—for instance, when Sendrel appears wearing his wife’s dress or when a dreaming Benjamin confides in a cow. But most of the book’s jokes are entirely deadpan: “In Tuneyadevka, indeed, there was a saying: ‘No matter what gossip starts with, it will end with someone’s death, and no matter what is debated, the price of meat will go up,’ thus accounting for the presence of death and taxes in the world, two things that only a heretic would question, although why everybody died while only Jews paid taxes remained an unanswered riddle.” Like all Abramovitsh’s jokes, this one is funny because it’s true: in Czarist Russia, Jews were taxed as a group through sky-high tariffs on kosher meat and other extortions. Another joke nails the absurdity of Jewish life that makes humor almost unnecessary. When Sendrel wonders who asked Benjamin to make this trip, Benjamin’s reply is initially delusional and then frighteningly rational: “ ‘What logic!’ jeered Benjamin. ‘I suppose the world asked Alexander the Great to go fight his wars in India! Do you think all the Jews roaming the world right now are being paid to do it?’ ”But the greatest blend of comedy and horror comes when Benjamin and Sendrel are kidnapped and sold into the Russian army—a common mid-nineteenth-century scam in which wealthy Jews would pay criminals to kidnap young Jewish men to fill conscription quotas. With their beards and sidelocks shaved, our heroes realize they are cannon fodder. As Benjamin points out to Sendrel, “If the enemy attacks, God forbid, are you and I going to stop him? … We’ll be lucky to get out of it alive. The way I see it, the army should be happy to be rid of us.” The army, however, disagrees; when Benjamin and Sendrel attempt to “push on with our expedition,” they are thrown in prison for deserting.At the court martial, Benjamin defends himself: “I see that kidnapping men in broad daylight and selling them like chickens in the market is permitted, but that when those same men seek to free themselves, they’re guilty of a crime! … We hereby declare, the two of us, that we are, have been, and always will be ignorant of all military matters, that we are, God be praised, married men with other things on our minds than your affairs, which are totally alien to us; and that we cannot possibly be of any use to you.” These words, Benjamin’s sanest, could be a summary of millennia of European Jewish history. What happens next is, therefore, predictable: the court martial is revealed to be a medical exam discharging Benjamin and Sendrel for insanity.The original Don Quixote concluded with Quixote recovering his senses and disavowing his delusions. But no one in the Jewish version disavows his delusions, ever. Instead, Abramovitsh promises us a sequel that will continue Benjamin’s journey to the Promised Land—which, generations later, is exactly what happened to many of those who escaped the shtetl alive. It’s funny because it’s true.